1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-[2-chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-urea

HRID 659014Notes

Reaction equation

HRID 659014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=2)[CH:19]=[CH:18][C:17]=1[NH2:31]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:31][C:17]2[CH:18]=[CH:19][C:20]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=3)=[CH:21][C:16]=2[Cl:15])=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 675239652-Chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine

Product 1

HCID 675240581-(4-Chloro-3-trifluoromethyl-phenyl)-3-[2-chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-ureaYield 26.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 281 mg (1.27 mmol) 4-chloro-3-trifluoromethyl-phenyl isocyanate in 3 ml THF was added within 5 min. drop by drop at 0° C. to a solution of 340 mg (1.27 mmol) 2-chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenylamine and stirring continued at r.t. overnight. The reaction mixture was evaporated and purified by chromatography on silica (ethyl acetate/isohexane 1:4) to give 162 mg (26%) 1-(4-chloro-3-trifluoromethyl-phenyl)-3-[2-chloro-4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-urea.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by chromatography on silica (ethyl acetate/isohexane 1:4)

Sources & evidence

ORD record
ord-5cfba7548b144640be00cc64810b95b4
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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